Flights from Chicago to Key West from $ 309*

Promotion Code

Changed bag rules and optional services         Cruise Packages

Featured daily fares for flights from Chicago (ORD) to Key West (EYW)

Mar 2026
From$ 375*
Viewed: 15 hours ago
RoundTrip|Economy
Apr 2026
From$ 309*
Viewed: 15 hours ago
RoundTrip|Economy
May 2026
From$ 309*
Viewed: 15 hours ago
RoundTrip|Economy
$ 309
$ 847
Displaying fares for March-2026
  • 17

    Tu

    MAR

  • 18

    We

  • 19

    Th

  • 20

    Fr

  • 21

    Sa

  • 22

    Su

  • 23

    Mo

  • 24

    Tu

  • 25

    We

  • 26

    Th

  • 27

    Fr

  • 28

    Sa

  • 29

    Su

  • 30

    Mo

  • 31

    Tu

  • 01

    We

    APR

  • 02

    Th

  • 03

    Fr

  • 04

    Sa

  • 05

    Su

  • 06

    Mo

  • 07

    Tu

  • 08

    We

  • 09

    Th

  • 10

    Fr

  • 11

    Sa

  • 12

    Su

  • 13

    Mo

  • 14

    Tu

  • 15

    We

  • 16

    Th

    • Range$ 309-$ 847

    *Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.

    More United deals on Chicago (ORD) to Key West (EYW) flights

    $
    keyboard_arrow_down
    More United deals on Chicago (ORD) to Key West (EYW) flights
    From
    To
    Fare Type
    Dates
    Price
    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		04/11/26 - 04/15/26

    from

    $ 309

    Viewed: 15 hours ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		05/06/26 - 05/13/26

    from

    $ 309

    Viewed: 15 hours ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		04/25/26 - 04/29/26

    from

    $ 309

    Viewed: 15 hours ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		04/08/26 - 04/15/26

    from

    $ 309

    Viewed: 15 hours ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		05/09/26 - 05/13/26

    from

    $ 309

    Viewed: 15 hours ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		09/26/26 - 10/03/26

    from

    $ 309

    Viewed: 2 hours ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		11/11/26 - 11/17/26

    from

    $ 309

    Viewed: 1 day ago

    Chicago (ORD)Key West (EYW)Roundtrip
    |
    Economy    		06/24/26 - 07/01/26

    from

    $ 309

    Viewed: 1 day ago

    *Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.

    Explore United Airlines's Top-Pick Destinations

    Explore more United flights